Gaylan Greenawalt
Product management coach for veterans and aspiring product managers
| Hourly rate range | $90 to $175 an hour |
|---|---|
| Focus areas | |
| Works with | Veterans |
| Also coaches | Executive coach |
| Credentials | Bachelor's degree in Quantitative Economics, United States Naval Academy |
Gaylan Greenawalt is a product management coach who helps people break into product roles and grow in them. He also coaches military and first responder veterans who want to move into tech. He worked as a product manager at LinkedIn, Amazon, Guideline and Airspeed. He served 11 years as a Navy officer and led teams of 30 to 100 people across 4 deployments. He now works as a senior product manager at Overland AI.
What Gaylan helps with
Gaylan helps people move into product management and tech. He also works on stakeholder management and building systems that scale.
- Breaking into product management
- Moving from the military or first responder work into tech
- Working in B2B SaaS and defense tech
- Chief of Staff roles
- Managing executive stakeholders
- Building team and organization systems that scale
Who Gaylan works with
Gaylan works with military and first responder veterans who want to move into the tech industry. He also works with people trying to break into product management. He coaches people aiming for Chief of Staff roles.
Background and qualifications
Gaylan graduated from the United States Naval Academy with a degree in Quantitative Economics. He served 11 years as a Navy officer. He led teams of 30 to 100 people through 4 deployments. He worked as a Navy-Senate liaison and as deputy chief of staff to the Navy's Chief of Legislative Affairs. In tech, he was a product manager at LinkedIn on Sales Navigator, at Amazon on Kindle Unlimited and Prime Reading, and at Guideline, where he led a team of 12. He also worked at Airspeed. He is now a senior product manager at Overland AI.
Gaylan Greenawalt pricing
Programs and services
- Product management coaching
- Chief of Staff coaching
Gaylan Greenawalt reviews
The CoachVouch take
He is a Navy veteran who moved into product management at LinkedIn and Amazon, so he knows the veteran-to-tech path firsthand.
Best for veterans and career changers who want to land a product management or Chief of Staff role in tech.
Common questions
How much does Gaylan Greenawalt charge?
Coaching with Gaylan runs $90 to $175 an hour. Message Gaylan from this page for an exact quote.
What does Gaylan Greenawalt help with?
Gaylan Greenawalt helps with breaking into product management, moving from the military or first responder work into tech, working in B2B SaaS and defense tech and chief of Staff roles.
Is Gaylan Greenawalt certified?
Gaylan Greenawalt lists: Bachelor's degree in Quantitative Economics, United States Naval Academy.
Does Gaylan Greenawalt coach military veterans?
Yes. He coaches military and first responder veterans who are moving into the tech industry. He is a Navy veteran himself.
How do I contact Gaylan Greenawalt?
Send Gaylan a message from this page. It's free and takes a minute.
Similar coaches to compare
Tick "Compare" to message several coaches at once.
Andy Fleischer
Andy Fleischer is a career coach who helps veterans and other professionals move into business, consulting, tech and top MBA programs. He began as a Special Operations Infantry Officer and led soldiers on three deployments to the Middle East. He then earned an MBA at Wharton and worked at L.E.K. Consulting. Today he leads a $1B+ business at Amazon. He has coached more than 60 clients through military transitions.
Brian Landry
Brian Landry is a management consulting coach who helps veterans and career changers break into top-tier consulting or the defense tech industry. He is a former Green Beret and 75th Ranger Regiment officer. He later consulted at Bain & Company and then moved into defense technology. He has made the move from military to consulting and from consulting to industry. Today he works as a business development manager for the Army portfolio.
Jonathan Javier & Jerry Lee
Jonathan Javier and Jerry Lee run Wonsulting, a career coaching company that helps job seekers from non-traditional backgrounds get hired. Coaches rewrite resumes and LinkedIn profiles, apply to targeted jobs for clients, and run mock interviews. The team includes former Fortune 500 recruiters and hiring managers. Wonsulting also offers a 120-day job offer guarantee and WonsultingAI, a set of AI job search tools with over 1.6M users.
William Chung
William Chung is an MBA admissions consultant who helps veterans and service members get into business school and move into tech. He is a Product Manager at Microsoft and a former Army MEDEVAC Black Hawk pilot. He earned his own MBA at MIT Sloan. He has helped 20+ people win acceptances at top 25 programs, including HBS, Stanford GSB, Booth, Columbia and Kellogg. He also coaches career changers into product management and product marketing.
Browse related
Last updated September 2026. Request a correction.